Methanol → HCID 73855136, compound

HRID 1242013Notes

Reaction equation

HRID 1242013 reaction equation
[CH2:1]([N:8]1[C:12](=[O:13])[C:11](=[C:14]2[N:18]([CH3:19])[C:17]3[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=3[S:15]2)[S:10][C:9]1=[N:24][C:25]1[CH:26]=[C:27]([NH:34][C:35]([CH2:37][O:38]C(=O)C)=[O:36])[CH:28]=[CH:29][C:30]=1[NH:31][CH2:32][CH3:33])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.O.C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl>[CH2:1]([N:8]1[C:12](=[O:13])[C:11](=[C:14]2[N:18]([CH3:19])[C:17]3[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=3[S:15]2)[S:10][C:9]1=[N:24][C:25]1[CH:26]=[C:27]([NH:34][C:35](=[O:36])[CH2:37][OH:38])[CH:28]=[CH:29][C:30]=1[NH:31][CH2:32][CH3:33])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 11430Potassium CarbonateHCID 73690429HCID 73690429, compound

Product 1

HCID 73855136HCID 73855136, compoundYield 21.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a 50 mL flask was added the product of Example 157 (0.19 g, 0.32 mmol), CHCl3 (5 mL), MeOH (10 mL), water (2 mL), and potassium carbonate (0.22 g, 1.6 mmol). After 4 h the reaction mixture was diluted with CHCl3 (40 mL), and the organic phase was partitioned, washed with water (20 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude sample was chromatographed (silica gel, 0–10% MeOH/DCM) to afford the title compound (37 mg, 21%). 1H-NMR (CDCl3): δ 8.14 (1H, s), 7.42–7.48 (3H, m), 7.27–7.33 (5H, m), 7.15 (1H, t), 7.09 (1H, dd), 6.99 (1H, d), 6.56 (1H, d), 5.15 (2H, s), 4.14 (2H, s), 3.71 (3H, s), 2.95 (2H, q), 0.99 (3H, t); MS(ESI): 546(MH+).

Workup

  1. customthe organic phase was partitioned
  2. washwashed with water (20 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude sample was chromatographed (silica gel, 0–10% MeOH/DCM)

Sources & evidence

ORD record
ord-7c780d9e79c7402daf1aa924882e0909
Source dataset
uspto-grants-2006_10
Patent number
US07115640B2

Reaction notes

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